Price found within the past 48 hours. Click for updated prices.

Arlo Chicago

Downtown Chicago

€476

per person

2 Jan - 6 Jan

found 18 hours ago

Return flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (1,852 reviews)

The room was really clean and the staff was very friendly and accommodating

Reviewed on 10 Nov 2025

Pendry Chicago

Downtown Chicago

€564

per person

2 Jan - 6 Jan

found 18 hours ago

Return flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

Very nice, service was stellar, the bed was super comfortable, location perfect for our activities. Bar and resturaunt inviting and comfortable. We will definitely return on our next visit to Chicago.

Reviewed on 9 Nov 2025

The Emily Hotel

Downtown Chicago

€580

per person

2 Jan - 6 Jan

found 18 hours ago

Return flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (1,248 reviews)

Really cool modern space

Reviewed on 4 Nov 2025

Tours & day trips

See all 157 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 49 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 26 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 12 activities

Rosemont: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

The 606

The 606 is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music and sunsets in the area.

Illinois Centennial Memorial Column

Learn about the local history of Chicago with a stop at Illinois Centennial Memorial Column. Stroll along the lakeside in this vibrant area or visit its top-notch restaurants.

Humboldt Park

Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theatre scene and entertainment choices in this vibrant area.

Humboldt Park Beach

Why not spend a lazy afternoon at Humboldt Park Beach during your trip to Chicago? Experience the live music and theatre scene in this vibrant area.

Logan Square Farmers Market

You can enjoy retail therapy at Logan Square Farmers Market during your visit to Chicago. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.

Concord Music Hall

Concord Music Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.